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Showing NP-Card for Methyl 3,4-dicaffeoylquinate (NP0335008)

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Record Information
Version2.0
Created at2024-09-10 23:28:41 UTC
Updated at2024-09-10 23:28:41 UTC
NP-MRD IDNP0335008
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl 3,4-dicaffeoylquinate
Description Methyl 3,4-dicaffeoylquinate was first documented in 2010 (PMID: 20822012). Based on a literature review very few articles have been published on Methyl 3,4-dicaffeoylquinate (PMID: 25172103).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335008 (Methyl 3,4-dicaffeoylquinate)


  Mrv2104 05262302002D          

 39 41  0  0  0  0            999 V2000
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -5.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -4.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817   -4.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -3.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935   -5.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  2  0  0  0  0
 16  4  1  0  0  0  0
 16  6  1  0  0  0  0
 16 12  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  2  0  0  0  0
 20 13  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  2  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 27 13  1  0  0  0  0
 27 14  1  0  0  0  0
 27 26  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 31 20  1  0  0  0  0
 32 23  2  0  0  0  0
 33 24  2  0  0  0  0
 34 26  2  0  0  0  0
 35 27  1  0  0  0  0
 36  1  1  0  0  0  0
 36 21  1  0  0  0  0
 37  2  1  0  0  0  0
 37 26  1  0  0  0  0
 38 22  1  0  0  0  0
 38 23  1  0  0  0  0
 39 24  1  0  0  0  0
 39 25  1  0  0  0  0
M  END
Download

3D MOL for NP0335008 (Methyl 3,4-dicaffeoylquinate)

Download
3D SDF for NP0335008 (Methyl 3,4-dicaffeoylquinate)

  Mrv2104 05262302002D          

 39 41  0  0  0  0            999 V2000
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -5.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -4.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817   -4.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -3.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935   -5.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  2  0  0  0  0
 16  4  1  0  0  0  0
 16  6  1  0  0  0  0
 16 12  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  2  0  0  0  0
 20 13  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  2  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 27 13  1  0  0  0  0
 27 14  1  0  0  0  0
 27 26  1  0  0  0  0
 28 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 31 20  1  0  0  0  0
 32 23  2  0  0  0  0
 33 24  2  0  0  0  0
 34 26  2  0  0  0  0
 35 27  1  0  0  0  0
 36  1  1  0  0  0  0
 36 21  1  0  0  0  0
 37  2  1  0  0  0  0
 37 26  1  0  0  0  0
 38 22  1  0  0  0  0
 38 23  1  0  0  0  0
 39 24  1  0  0  0  0
 39 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335008

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)CC(O)C(OC(=O)\C=C/C2=CC(OC)=C(O)C=C2)C(C1)OC(=O)\C=C/C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1/C27H28O12/c1-36-21-12-16(4-8-18(21)29)6-10-24(33)39-25-20(31)13-27(35,26(34)37-2)14-22(25)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h3-12,20,22,25,28-31,35H,13-14H2,1-2H3/b9-5-,10-6-

> <INCHI_KEY>
RTLCSWCXZWROFK-OZDSWYPANA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.627501877770214

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

> <JCHEM_LOGP>
2.450018428666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.950856825029973

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.122152272650792

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2468836164082338

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999994

> <JCHEM_REFRACTIVITY>
136.01559999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0335008 (Methyl 3,4-dicaffeoylquinate)
Download
PDB for NP0335008 (Methyl 3,4-dicaffeoylquinate)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      14.671 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.092 -10.902   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.185  -8.236   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.646  -8.182   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.462  -6.984   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      14.671 -10.010   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.908  -9.596   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
CONECT    1   36                                                            
CONECT    2   37                                                            
CONECT    3    7   15                                                       
CONECT    4    8   16                                                       
CONECT    5    9   15                                                       
CONECT    6   10   16                                                       
CONECT    7    3   17                                                       
CONECT    8    4   18                                                       
CONECT    9    5   23                                                       
CONECT   10    6   24                                                       
CONECT   11   15   19                                                       
CONECT   12   16   21                                                       
CONECT   13   20   27                                                       
CONECT   14   22   27                                                       
CONECT   15    3    5   11                                                  
CONECT   16    4    6   12                                                  
CONECT   17    7   19   28                                                  
CONECT   18    8   21   29                                                  
CONECT   19   11   17   30                                                  
CONECT   20   13   25   31                                                  
CONECT   21   12   18   36                                                  
CONECT   22   14   25   38                                                  
CONECT   23    9   32   38                                                  
CONECT   24   10   33   39                                                  
CONECT   25   20   22   39                                                  
CONECT   26   27   34   37                                                  
CONECT   27   13   14   26   35                                             
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   20                                                            
CONECT   32   23                                                            
CONECT   33   24                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36    1   21                                                       
CONECT   37    2   26                                                       
CONECT   38   22   23                                                       
CONECT   39   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

Download
3D PDB for NP0335008 (Methyl 3,4-dicaffeoylquinate)
Download
SMILES for NP0335008 (Methyl 3,4-dicaffeoylquinate)
COC(=O)C1(O)CC(O)C(OC(=O)\C=C/C2=CC(OC)=C(O)C=C2)C(C1)OC(=O)\C=C/C1=CC(O)=C(O)C=C1
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INCHI for NP0335008 (Methyl 3,4-dicaffeoylquinate)
InChI=1/C27H28O12/c1-36-21-12-16(4-8-18(21)29)6-10-24(33)39-25-20(31)13-27(35,26(34)37-2)14-22(25)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h3-12,20,22,25,28-31,35H,13-14H2,1-2H3/b9-5-,10-6-
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Synonyms
ValueSource
Methyl 3,4-dicaffeoylquinic acidGenerator
Chemical FormulaC27H28O12
Average Mass544.5090 Da
Monoisotopic Mass544.15808 Da
IUPAC Namemethyl 3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate
Traditional Namemethyl 3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1(O)CC(O)C(OC(=O)\C=C/C2=CC(OC)=C(O)C=C2)C(C1)OC(=O)\C=C/C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1/C27H28O12/c1-36-21-12-16(4-8-18(21)29)6-10-24(33)39-25-20(31)13-27(35,26(34)37-2)14-22(25)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h3-12,20,22,25,28-31,35H,13-14H2,1-2H3/b9-5-,10-6-
InChI KeyRTLCSWCXZWROFK-OZDSWYPANA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.45ChemAxon
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.28 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity136.02 m³·mol⁻¹ChemAxon
Polarizability52.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Chen J, Mangelinckx S, Ma L, Wang Z, Li W, De Kimpe N: Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast alpha-glucosidase and PTP1B inhibitory activity. Fitoterapia. 2014 Dec;99:1-6. doi: 10.1016/j.fitote.2014.08.015. Epub 2014 Aug  27. [PubMed:25172103  ] 
  2. Liu J, Ding G, Yu S: [Chemical constituents from stem barks of Vernonia cumingiana]. Zhongguo Zhong Yao Za Zhi. 2010 Jun;35(11):1421-4. [PubMed:20822012  ]